Camp Chitaqua
by Switzerland1996
Summary: Starts in the episode The End and weaves its way into a giant mess the Winchesters have to fix up before Lucifer turns everything into what Dean saw on his vacation. Sydney, OFC, may just be a distraction. With secrets, lies, and crushes I hope you enjoy!
1. Blast to the Past

**Alrighty, forewarning you here, um...this is pretty much along the lines of the episode 'The End.' So, please read, but mind you, there are parts from the episode I took word for word, or close to it. I just wanted to introduce my character into the story. Next chapter, if you guys want me to, will be different and what not. I will have Sydney, my OFC, in the past back where she belongs and meeting Dean and Cas alongside that road at the beginning/end of the episode.**

**Disclaimer: Not mine, even though I offered Sara and Eric my fanfic account and a poster of Jacob Black (Twilight). They refused, and threatened to get a restraining order if I didn't leave them alone.**

**I hope you guys enjoy! (:**

Everyone at Camp Chitaqua was pretty tough. If you walked up to any of the girls with a flirty comment and an offered beer, when they were sober, you'd probably get a punch in the face and marked as an asshole. (It was a different story once they'd drank a few beers and done a few shots, though.) The men were all pretty much running on empty their whole lives when the Croats started coming. Nonstop fighting, drinking, sleeping, and eating, there was no time for love and 'connections.' Everyone was pretty tough, except for one girl. She was close to Dean, the fearless leader of Camp Chitaqua, before the Croats started eating people's faces. She met him in 2009 after a bad run in with a werewolf. She allowed him to patch her up and they began hunting together. She helped fill in the void Sam had made.

Ah…Sam, the youngest – full-blooded – Winchester. He was on the 'don't talk about unless you want to get stabbed in the jugular' list. Dean made that list. Not even girls could talk about Sam, not to Dean at least. They would receive quite the ass chewing before Dean would try and exile them from the camp. Castiel, the angel friend who stayed with Dean through it all, wasn't even permitted to talk about Sam.

Castiel - the unlabeled guy of the group. He was sort of a stress reliever for the women. He loved them, and promised not to leave them. All of the women had stopped by Castiel's cabin at least once, just to experience the kind of love only an ex-angel can give. Yeah, that's right, Castiel lost his wings. They were clipped right off when the angels pulled out, so to speak, but the semi-angel was still loyal to Dean. Dean said jump and Cas said how high. They were friends, Castiel had tried to reason to Heaven once, but they just didn't understand his point.

Back to the girl, her name was Sydney Nicole Matthews. She stuck around the camp, teaching kids the importance of a balanced diet and exercise, as well as the history that she could still remember. She had been quite the history buff, and when Dean had come to her that night when the Croats over took the world, she had packed her two duffle bags to the rim with books and toilet paper. Laugh now, but when the Apocalypse is kicking, you'll really wish you had hoarded the stuff.

She walked around the camp, kicking dirt and staring off into space too often. Some people called her a freak, a weirdo, because she always smiled and tried to make light of every situation. Some even flat out ignored her presence, called her evil and wanted to kick her out of the camp. Dean never let it happen, because even if he had had his fair share of hatred towards the only woman in the camp that hadn't turned into a rock, he still had feelings toward her.

She never joined in the hunts, didn't touch guns, and didn't want to help put up spells and junk. She knew how to, better than half of the camp, but she wasn't going to turn into a girl like Riesa or Jane. Riesa was always walking around with her arms crossed and a sour face locked on. She was quite a bitch, actually. Jane was similar to Riesa, only a tad softer than her. Jane was still a hard ass, though. She even got to go on some of the missions that Dean set up.

The only time Dean talked to Sydney anymore was in the group meetings, where he was required to tell everyone everything was going to be okay, and he was going to make sure everything stayed okay. She always listened quietly, never interrupting like others. At the end of the meetings she never bombarded him with questions and accusations like everyone else. She just sat back and watched as he slipped from 'trying to help' Dean to 'brooding and hateful' Dean.

Sydney hadn't ever been with Castiel, but they were friends. She sat in some of his meets, and always left when the orgies were about to begin. One time, maybe a Thursday, she was sitting on the floor next to Castiel, listening to him appreciatively, when the beaded curtain was swept to the side. Dean walked in with his blue over coat and a confused expression etched on his face.

Castiel smiled and said, "Excuse me, ladies, I think I need to confer with our fearless leader for a minute. Why not go get washed up for the orgy?"

She watched Dean's eyes widen at the mention, and then all the girls began filing out. Sydney stayed put, only standing up with Castiel. Dean eyed her while saying to Castiel, "What are you, a hippie?"

Castiel stretched his arms behind his back with an annoyed look on his face, "I thought we'd gotten over trying to label me."

"Cas we gotta talk…"

"Whoa," Castiel's eyes widened as he eyed Dean. "Strange…"

"What?"

"You," Castiel blinked. "Are not you, not now you, anyway."

"No! Yes, exactly," Dean stumbled.

"What time are you from?"

"October, 2009," Dean started as her heart sank. He wouldn't know who she was; he wouldn't have any inkling what they had been through together. He was just going to be another Dean Winchester that broke her heart unknowingly. As tears welled up in her eyes she shouldered pass the two men and slipped out of the beaded curtain.

"What's up with her?" Dean watched her walk out, having saw her eyes fill up with tears.

"You don't know her yet, but in 2009 you meet Sydney after a werewolf attack. She's probably upset that you don't know her, so you're just going to be another Dean Winchester that ignores her every movement in existence. So, who did this to you? Is it Zachariah?"

"Yes," Dean answered, ignoring most of what Castiel said. Some random girl he may or may not meet in the past/future? wasn't much of his concern at the moment.

Castiel touched his finger to his chin thoughtfully, "Interesting…"

"Oh, yeah, it's freakin' fascinating. Now, why don't you strap on your angel wings and fly me back to my page on the calendar."

Castiel laughed, almost condescendingly so, and barked out, "I wish I could just, uh, strap on my wings, but, uh, I'm sorry. No dice."

"What are you? Stoned?" Dean looked at him sideways, watching his old friend laugh.

"Ehh, generally, yeah," Castiel nodded.

As the two wrapped up their conversation, Castiel telling Dean what had happened to his wings and his powers, Sydney stood outside, watching Dean pull up in his Jeep. The one man in the whole camp who had ever actually talked to her without ever having a single notion she was crazy, excluding the ex-angel in the cabin behind her. Past-Dean came out of the beads just in time to see Present-Dean cracking a cold one open for him and Yeager.

Larry Yeager was a good man, before the virus he had a wife and two children. When they were mauled to death in front of him by twisted humans, or Croats, Larry turned a little to the sideways. Larry was one of Dean's friends, as close as a friend you can get when building relationships only means hurt. Larry was always on the frontline, ready to defend and conquer when Dean asked. It was pretty shocking to see Present-Dean pull out his gun and cock it.

As Past-Dean shouted out a warning, and Larry turned around, Present-Dean shot Larry. The two men who had been with Larry and Dean on the mission didn't bat an eyelash at Present-Dean's actions, but Past-Dean was gawked at. As Present-Dean gave a shaky explanation about whom and what Past-Dean was, the two men turned to leave as ordered. If Dean, their honest to God, (if you still believed him at that point) trustworthy, leader, said there was nothing to know, there probably wasn't.

Sydney followed close behind as Present-Dean shoved Past-Dean into his cabin. "What the hell was that?" Present-Dean demanded as Sydney closed the door behind the two.

"What the hell was that? You just shot a man in cold blood," Past-Dean accused.

The two argued slightly, not the worst argument Sydney had ever seen either Dean's have. While Present-Dean poured the two a drink, Past-Dean eyed Sydney. Present-Dean sat down the glasses, not bothering to offer Sydney one because he knew she wouldn't accept it. Her father had been an alcoholic, and she wasn't going to turn into one either. Who knows if it's genetic? She wasn't taking the chance, not even on her last day on Earth.

"What's the deal with her?" Past-Dean questioned, nodding towards Sydney.

"She's a friend," Present-Dean said, sipping his drink and watching Sydney closely.

Sydney nodded shortly at Present-Dean, telling him she wasn't going to spring her life story on Past-Dean if he didn't want her to. Past-Dean turned to Sydney and then back to Present-Dean, "Castiel said something about us hunting with her before all this went down."

"Of course he did," Present-Dean snorted, rolling his eyes. "We use to hunt with Sydney, yeah, she's damn good at it, and that's all you need to know. When you meet her in your time, you can talk all you want."

"Fine," Past-Dean relented. "What was the mission for, anyways?"

Present-Dean unzipped his duffle bag and pulled the Colt from the depths. Sydney's breath caught in her throat, he had found it. It was a large victory for the team. She licked her lips and looked up at Present-Dean as he told Past-Dean his plans for tonight. He was going to kill the Devil. More horrible news for the girl. She spun on her heel, and walked out of the room, it just wasn't her day. She was going to watch her best friend, her trusted ally, the love of her life, kill his brother.

Of course she was going to go with, if there was ever a chance to say goodbye to Sammy Winchester, the Winchester she met before Dean, then she was taking it. She found Castiel and Riesa, rounding them up for the upcoming meeting she knew was going to happen. Riesa was a bitch, just like always. She looked at the gun unsatisfactorily, "So, that's it. That's _the_ Colt."

As the meeting waged on, and Sydney watched as Past-Dean informed Present-Dean of their whereabouts last night, she sighed. When the torture subject came up, she watched Past-Dean become upset. She knew he hated himself for torturing Alistair after coming back from Hell. She knew he hated himself for torturing people period. When Riesa and Castiel left, Sydney folded her arms across her chest.

"Why are you taking him?" she questioned, turning her back on Past-Dean to watch Present-Dean pack his duffle.

"Relax, he'll be fine. Zach's watching over him," he sighed.

"Dean, you don't want him to see this, do you?"

"See what?" Past-Dean cut in, eyeing the two.

"Our brother," Present-Dean walked around the table to stand in front of his clone.

"I thought he was dead," Past-Dean frowned.

Present-Dean looked over at Sydney, and then walked back to his bag. He swung it over his shoulder and walked out of the room. She knew what he had meant when he looked at her. She grabbed Past-Dean's arm to stop him from following Present-Dean out the door. "Is Sam dead?" he looked down at her.

"No," she shook her head. "He didn't die in Detroit…he said yes."

"Yes?" Dean repeated, her hand falling from his arm.

"Right to Lucifer, in front of God and everyone," she sighed, pulling out a chair out for herself. She collapsed on the brittle wood and rubbed a hand over her face. "I'm sorry, Dean, I really am."

He sat down in the chair opposite her. He sat his hands flat on the wooden table and asked, "What happened? Between us, I mean. Everyone's acting like we were in some sort of relationship or something, but you and, uh…future-me, you don't seem so in love."

She half smiled and shook her head, "It's a long story, really."

"Well, I've got time," he shrugged.

"Honestly, it doesn't even matter anymore. I kind of got this crazy idea in my head that, maybe, just maybe, me and you could be together some way, somehow, but it just isn't, wasn't, going to happen. I don't mean to be rude to you, Dean, I'm sorry. It's a sore subject, even two years later," she rolled her eyes at herself.

"If that was rude, you must just be about the nicest person in the universe," Dean chuckled, picking up the glass with the liquor still swirling around.

She leaned forward against the table, and grabbed Dean's hand suddenly. He looked shocked, but didn't try to pull his hand back. "Dean, I never wanted Sam to get hurt. I…I know I haven't said this yet, but when I do say it, just so you know, I don't mean it. I love Sam, I love Bobby - I love all of you guys. I was just being a bitch, and I hate myself, still, for saying it."

"What did you say?" Dean frowned, setting his cup down.

"I-I called Sam a demon," she winced. "I'm so sorry, I never meant it. I just got scared, I got scared you were going to leave again and I never meant for you to-to have to go do that by yourself."

"Do what?" he questioned, hand trying to fall from hers.

"Go to Detroit by yourself, face that show down by yourself… I should have been there, and I am so sorry," she dropped his hand as the door opened.

"What are you doing?" Present-Dean walked in, eying the two. He noticed her torn expression, and his clone's confused one. "Are you telling him about us?"

"No," they both answered.

"What'd you say?" he crossed his arms.

"Nothing," she stood up, walking to the door Present-Dean was blocking.

"What did you say, Sydney?" he repeated, voice going lower, scarier.

She locked her jaw, and picked at an invisible piece of lint on her shirt. "I didn't say anything, Dean. Just let me go get my things together."

"Together for what?"

"For tonight," she looked up at him.

"You aren't going," he shook his head.

"What? You don't expect me to let you do this alone, do you?" she exclaimed.

"No, I don't. Cas and Riesa, and a few others are helping. You are staying here. You are going to run this camp unless I don't come back, but sure as _hell_ are _not_ coming with on this Kamikaze mission!" his voice shook.

"Yes, I am, Dean," her voice stayed level and calm. "I won't leave you to do this by yourself, not again." Her mouth shut tight and she backed up. "I-I'm sorry, please, just let me go."

Present-Dean seemed to remember Past-Dean was sitting at the table, watching them, and he quickly snapped his mouth shut as well. His jaw locked tightly and he opened the door for her. She walked out and jogged down the stairs before going to her cabin two places down. He closed the door behind himself and turned back to his clone.

"What was that?" Past-Dean demanded, standing up.

"That was Sydney, you'll be dealing with her for the next five years of your life, man," Present-Dean shook his head.

"What?"

"That girl has got us so-so messed up, we don't even know left from right when she's around. You'll see, when you meet her, it's gonna be the best day of your life. And then Hell from then on out. She's a whirlwind of emotion, but she's the nicest damned woman you'll ever meet," Present-Dean grabbed a bottle of liquor and took a swig. "I hate her for it."

"I'll say it again, _what_?"

"I don't know, man, she-she is such a damn… She's so… She's the best thing that ever happens to us, better than, than that Lisa girl, the yoga instructor. She makes everything okay, even when Lucifer is roaming Earth, even when Cas loses his wings, _even_ when we're contemplating putting a bullet through our head. She's always there to make sure we're okay… And we go and screw it all up, like we always do."

"Apparently she wasn't there in Detroit," Past-Dean said quietly.

"And that was our fault! She still blames herself, damn it, but we were the ones that did that! We completely took it out of context and did what we always do when someone gets too close! It was _never_ the same after we left. She _never_ trusted us again, and probably never will!"

"Is that how we screwed it up? We walked out when she called Sam a demon?"

"Yeah," Present-Dean scrubbed a hand over his face, eyes tired. "Yeah, she called him a demon, but it's not like we hadn't said it before. Not like Cas didn't say it, Bobby didn't insinuate it, not like we tried to get her to see it our way, try and get her to understand why Sam couldn't be saved and she should just give up on him. We're the ones that pulled the plug on that gig; it's always our fault, man."

"Dude, sounds like we're a dick starting real soon," Past-Dean laughed.

"Yeah, we really are," Present-Dean sighed. "We really are."

After the little heart to heart with, well, himself, Present-Dean left his cabin, telling his clone to try and stay put this time. Dean walked over to Sydney's cabin and leant against the door jamb. He listened quietly and could hear her sniffling on the other side. He'd made her cry, again. His past self coming back was really jacking up his feelings. He knocked on the door and almost instantly her sniffles were silenced. With a perfectly normal voice she called through the door, "I'll be out in a minute, Cas, I've just got to, um, get some stuff for, uh, the meet tomorrow."

"It's Dean," he answered back.

"Oh." He could hear her moving around in the room. "What do you want?"

"Can I, uh, come in?"

"I-I don't think that's a good idea right now, Dean," she sighed.

"C'mon, Syd, we need to talk," he shifted against the jamb.

Maybe it was him using her nickname for the first time in years, or maybe she just really wanted him to hold her, but the door opened slightly and Dean walked inside. She was sitting crossed legged on her bed, staring at the floor. Dean closed the door behind him and coughed uncomfortably. He stepped into the room a few steps and looked around. She could really use some new lighting and maybe some new furniture. He'd see to it someone had that taken care of before he left.

"I'm sorry, Dean, it wasn't my place to tell your past self all that," she tucked her hair behind her ear.

"I'm not mad," he ran a hand through his hair.

"Yeah you are, you're mad at me because I can't stop apologizing for what I did all those years ago, but I still feel terrible."

"Don't, seriously, I have never and will never blame you for not coming with. It was my fault, my doing - so just stop saying you're sorry. It's all on me," he sat in the chair in front of her bed.

"Dean-" she was cut off by a knock at the door. "Yeah?" she hollered, closing her eyes. She finally gets Dean alone, her Dean, not the cold hearted one she had seen walking around for a few years, and she gets interrupted.

"It's Cas," the ex-angel replied.

"Come in, Cas," she sighed.

"Ah, Dean, you're in here too. Did I interrupt something?"

"No, what is it?" Dean snapped back into the icy hearted man he was just ten minutes ago.

"Jane is looking for you, she would like to come with," Cas smiled.

Sydney stood up and started for the door. "Wait, Sydney, we should finish talking," Dean craned his neck around Castiel.

She just slipped out the door, not wanting to hear anymore about Jane or Riesa or any other girl he had screwed. Not any other girl that Dean would let goes on hunts, but not her. Not any other girl that Dean eyed appreciatively when she was just pushed aside like a rag doll. It was bull, and everyone knew it. Everyone knew that Dean and she had been an 'item' before the Croats. But no one seemed to care.

As she was ranting in her head, she didn't notice Past-Dean come up behind her. "Hey," he greeted, making her jump. "Sorry," he half smiled.

She looked up at him, watching the light in his eyes dance. He was happy, still alive, still warm…she hated him for it. She swung her fist back and clocked him in the eye. "You son of a bitch!" she nearly screamed.

"Whoa, whoa, calm down," he tried.

"You God damned asshole!" she tried to punch him again, but he caught her arm.

"Stop, stop," he twisted her around, but she broke from his hold.

She kicked him in the shin while shouting, "You are such a freakin' jerk! I hate you!"

The cabin door she had just left swung open and Present-Dean watched as Past-Dean received another punch to the face. "Hey!" he called, jumping from the deck and down to his past self's rescue. "What the hell are you doing, Sydney!"

"Screw you!" she shouted. "You are such-such an asshole, Dean! I hate you, both of you!"

"What did I do? We do?" Past-Dean looked up at his future self from his kneeling position on the ground.

"I don't know."

"Oh, you don't know, right," she said sarcastically. She flicked her eyes to Castiel and then to the growing crowd watching. She stepped back, not happy with making a scene. "I am _not_ sorry about this, Dean. And I _am_ going, damn it. I _am_ going with, so don't you _dare_ try and stop me."

She turned on her heel, leaving no room for discussion, and stomped over to the other side of the camp, slamming the door to the school house behind her. Present-Dean looked out at the crowd and shouted, "There's nothing to see here! Back to work, people!"

They dispersed almost immediately, and Present-Dean helped Past-Dean up. "What the hell was that?" Past-Dean demanded. "What did you do?"

"I told her it wasn't her fault, and she flipped out. Actually only the second time I've really seen her get mad," Present-Dean seemed to be in awe.

"Yeah, that's all great and dandy, but you're not the one that just got his ass kicked," Past-Dean rolled his eyes.

"She's a girl, you could have taken her," Present-Dean dismissed him.

"Yeah, but she's a girl. Unless she's possessed or a monster, I don't hit girls," Past-Dean wiped his lip.

"You're different in 2014, man," Present-Dean admitted, and turned from the slightly stunned expression on Past-Dean's face.

As midnight rolled around, both Dean's began loading up the truck. Three cars were packed with a team, and Sydney rode in the one that didn't hold any Deans. As they trudged through an empty and abandoned set of streets, Sydney hung in the back, a gun around her chest and one in her hands. She had a duffle bag on her shoulder and her combat boots back on. A low sun peeked through the clouds, and Sydney took a deep breath.

Today, she was going to lose her family. Dean was going to go in there and try to use the Colt on Lucifer aka his brother. He was going to let his past self watch, and then she was going to be alone, because goodness knows no one else was going to make it out. These people were under trained, weak, and scared, and Dean wasn't going to be able to save all of them, and kill the devil. Castiel was always useful when he had his powers, but since then, he'd just lost faith in himself.

She ducked down behind the blue car and hugged her gun close to herself. "You sure about this?" Riesa questioned, and she just wanted to punch her in the face. Doubting a leader? Let alone _the_ leader, seriously?

As Past-Dean and Present-Dean argued behind a set of trees, Sydney chambered a bullet and grabbed out her extra ammo to set around her chest. She rotated her neck and looked over at the others. Castiel knelt in the dirt, holding a small gun, and Riesa sat next to him, determinedly checking her weapons as ordered. Dean was lying to these people, and his past self was probably telling him such right then. She knew he was lying, she'd seen him use that face to tons of police officers, agents, angels, demons, monsters, himself…

She swallowed thickly as she wondered which team she would be on. Would she be sent in like a decoy like the others, or would she get to be in on Dean's secret team? She watched as Present-Dean knocked out Past-Dean and then came over to the group. "Sydney, you stay here with him, watch him until he wakes up. Make sure he doesn't get eaten by a Croat. The rest of you, here's the game plan," and Dean explained to them that he was going to go in through the back, and the rest to the front. They knew what he was doing, but none spoke out loud.

She watched Dean slowly wake up and closed her eyes at the nosy gun fire from inside the building. At an instant, without even so much as a glance to her, Dean began running towards the building. They ran to the back, no words spoken, and as they entered the court yard, she saw Sam's foot around Dean's neck. Well, not Sam's…Lucifer's.

Lucifer turned around and half smiled, "Oh, hello Dean. Sydney, nice to see you again."

He winked at her and she gritted her teeth, "You son of a bitch!"

"Aren't you a surprise," Lucifer remarked, ignoring her. Dean and Sydney both flinched as the lightning lay siege.

Lucifer blinked to behind them, and Dean sighed, resigned, "Go ahead, kill me."

"Kill you? Don't you think that'd be a little…redundant?"

As Lucifer spoke to Dean, Sydney walked around the duo and to her Dean's side. She pressed light touches to his neck, felt the bones peeking through his skin, and felt that wall that she had fought for so long start to strengthen. He was dead, the only tie to Earth she had, and he was gone. She had no one, the man behind her was going to be sent back to his time in a matter of minutes, and she would be alone.

The lightning grew more haywire as Lucifer made his parting comment and Dean and her stood in the court yard alone. Dean looked down at her where she knelt by his future self and said, "I'm sorry," just before Zachariah appeared and touched his two fingers to Dean's forehead, zapping him back to the past.

**So, drop me a line. Was it good? Did it suck? Next chapter, if you guys would like, will be my story line instead of the shows. I will say, just so you know, Sammy is in this story, and not just as Lucifer. Alright, I'll leave ya to it! Please review, pretty please! With all the ice cream toppings and Sam and Dean on top! (:**


	2. Kisses & Keith

**Okay, so…here's the next chapter. Thanks to everyone who read last chapter and this chapter! Please leave me a review when you finish this chapter! Thanks!**

**STORY ALERT THANKS:**

**adaddario**

**Christina5139**

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**I appreciate everyone, and I really hope for some reviews! (:**

As I ran, panting, through the biggest forest in the freakin' world, I spotted two men talking by a road. One wore a tan trench coat and the other wore a blue over coat, neither seemed to really notice me until I broke the clearing. The trench coat turned and stared at me, calculatingly, and the other stared with his mouth agape. The trench coat turned to his friend and back to me, "Do you know this woman, Dean?"

"You're bleeding," Dean pointed out, nodding to my shoulder.

"What road is this?" I licked my lips, not happy to find two civilians in the middle of the night.

"Uh, Interstate 49, why?"

"Listen, you two need to get as far away from these woods as possible, alright? There's something in there that did this to me, and it'll do far worse to you, got it?"

"What is it?" Dean questioned.

"You wouldn't believe me even if I told you," I rolled my eyes, moving my arm closer to my body.

"How bad is your wound?" he changed the subject again.

"Deep, I'll need stitches, but you need to get out of here. Seriously, get in your car and drive away."

"What? Why?"

Before I could answer a growling was heard behind me. I sighed and turned around just as the beast was jumping mid air, I pulled out my gun from my pants and shot it in the face before it could land on me again. Dean let out a, "Holy crap!" as I turned back around and said, "I'm sorry you had to see that."

"Was that a werewolf?"

I stared at him for a long second before saying, "Are you two hunters?"

"Yeah, are you?" he questioned.

"Yes," I rolled my eyes, putting my gun away. "Can I get a little help here? It got my arm, and leg, think you can burn it and get me some stitches?"

"Pretty trustworthy for a hunter," he said, we'd gotten the werewolf burnt and me patched up. We were in a motel room, the trench coat still hadn't said his name, but Dean kept calling him Castiel. I stood up from the bed and said, "Yeah, sure, well, thanks for the help. I better get going."

"Wait," he said too quick and loud for it to be casual.

"Yeah?"

"Well…don't you want to stick around?"

"Why?" I cocked an eyebrow. "We barely know each other."

"Because…I want to get to know you?" he suggested.

I eyed him, wondering if I could trust him, and shrugged, "Why not, not like I don't deserve a drink after that."

"But…I have to do something first," he stood up, pulling out his cell phone.

I watched as he dialed a number and spoke to someone. When he hung up, he said, "I have to go meet my brother, can we meet up sometime?"

I laughed slightly, "This might be the weirdest hunt I've ever been on." I scribbled my number down and handed it to him, "When you get a chance, call me."

I slipped out the door, and as I walked by his car, I couldn't help but think… Damn that car looks familiar.

When Dean called me, he was in Canton, Ohio. He has just solved a case and he wanted to meet up, wherever I was, he said he'd drive out. I laughed, and said, "Dean, I'll be in Ohio in an hour. What bar?"

So we met up at a bar, and when I walked in, it wasn't hard to find him. He was in the back, jacket on, and a beer in front of him. He grinned when I walked in, and I sat down across from him. "How have you been? It's been a whole…week, since we met."

"Yeah, sorry about that. Me and my brother…we took a break from hunting together, we had to get back on track," he sighed, sipping his beer.

"I was kidding," I laughed. "Might be the fastest someone's ever called me back, especially when we first meet is right before I shoot a werewolf in the face."

"Yeah…that was pretty badass, by the way, good job on that," he grinned.

"Good job on stitching me up, no scar whatsoever," she smiled.

"Still can't believe you didn't even drink anything while I did that, tough cookie," he sipped his beer again. "Do you want anything?"

"No, I don't drink," I shook my head. "Dad was an alcoholic; don't like to risk the chance if it's genetic."

"Oh, uh, sorry," he looked down into his beer before scooting it away.

"Don't be," I laughed. "So, Dean, why did you invite me out here? I mean, you still don't even know my name."

"Well, what's your name?"

"Sydney," I stuck my hand out. "Sydney Matthews, pleasure to meet you."

"Dean Winchester, pleasures all mine," he grinned, shaking my hand.

As we dropped our hands, I shifted in the booth. "Dean, why _did_ you invite me out here?"

"This is going to sound crazy-"

"We're both hunters here, Dean," I scoffed. "Probably no crazier than the usual."

"A tad," he licked his lips. "Do you believe in angels?"

"Of course, all church going people do," I nodded.

"Well, Zachariah, he's an angel, sent me into the future five years from now," he started.

"Why?" I trailed cautiously.

"To show me what the 'path of life I'm living' is going to do," he continued.

"And…" I nodded for him to go on.

"And my future self and you were…had been together before, like, in a relationship. And my future self told me things about you that, well…they made me want to really meet you," he coughed uncomfortably. "No idea where that came from, sorry."

"Angels?"

"Yeah, the, uh, guy in the trench coat, tax accountant looking guy," he started and at my nod, continued. "Angel. His name is Castiel."

"Castiel? Wow," I blinked. "Weird name."

"You're taking this surprisingly well," Dean blanched.

"Yeah… After awhile surprise isn't really an emotion," I laughed. "It's just easier to accept it than question the hell of it."

"Yeah, I suppose so," he allowed. As silence fell over us, I scratched at the back of my head and looked around the nearly empty bar. I looked to the back of the bar to the pool tables and turned back to the hunter across me. "Wanna play some pool?"

"Not sure it'd be fair, darlin'," he drawled in a voice that hinted at a southern heritage. "I hustle pool for a living."

"Well, I promise to go easy on you," I chuckled, and stood up, sauntering over to the pool table and racking up the balls.

He ended up winning, of course, because he cheated every chance he got. When he struck the final ball into the pocket I swung accusing eyes on him and protested, "You cheated!"

"How you figure that?" he laughed.

"I'm not sure yet…but when I figure it out, I'll be sure to tell you," I shoved the stick up on the rack. "I hate losing."

"Ah, so you're a sore loser?"

"Only naturally," I grinned. "I'm a hunter, after all. I don't lose in that gig."

A question fluttered across his face, and as he bit his lip, I could see him getting ready to voice his confusion, but I just placed the triangle up next to the stick and said, "It's getting late, Dean. I should get back to my place. It was great seeing you."

"It's only eleven," he pointed out. "Not very late."

"Well what else is there to do at a bar?" I smirked.

"Who said we have to hang out here? We could go back to my place," he offered.

"And you think I'm that easy, why?" I stepped closer to him, leaning against the table.

"You're the one that went that way, I was talking about some television, maybe a round of cards," he shrugged, cocking an eyebrow as he stepped closer.

"I'd win in cards, guaranteed," I licked my lips, looking up into his eyes.

"Wanna bet?" he challenged.

"Damn straight," I walked pass him, slapping his ass on the way. "Come on, big boy! You're leading!"

That night I left Dean's motel room without ever having to remove my clothes. As I stepped across the threshold of his room, and he leant against the door jamb, I looked up at him. "What was it like in the future, Dean?"

He looked over my head, out into the dark, and shook his head shortly. He looked back down at me and shrugged, "Not like this."

I dropped my gaze to his shoes and nodded slowly. His finger slipped under my chin and raised my eyes back up to his. He leaned closer, and I pressed up on my tip toes, and our lips met. It was all electricity and bells. His lips were soft and moved softly against mine, not the way I had expected, but it was a pleasant surprise. I licked at his bottom lip and when his mouth slipped open it was his tongue penetrating my mouth.

A man that takes charge, just what I was looking for.

As his tongue scoped out my mouth, and my hands reached up around his neck, we didn't even notice the person walking up behind us. It wasn't until the man cleared his throat that our lips broke and I spun around to face the giant. He was huge! He had long, chestnut hair, and long limbs. He shared a nod-greet with Dean, and then turned to me.

"Keith?" I cocked my head to the side.

"Who?" Dean looked up at the man while Sam scratched at his head awkwardly.

"It's, uh, Sam, actually," he smiled slightly.

"Oh, okay, sorry. I just thought…I mean, you said your name was Keith, right?"

"Yeah, um, it's a long story," he looked over at his brother uncomfortably.

"_Sam_, this is Sydney, a friend, Sydney, this is _Sam_, my brother," Dean said slowly.

"Right, right, we know each other, actually. When we, um, split up, I met her at the bar I was working at," Sam revealed.

"Oh."

"Um, I was just coming by to tell you Cas called."

"Cas? What'd he say?" Dean stepped out of the room.

"Uh," he flicked his eyes to me and then back to his brother.

"Oh, I'm sorry, I was just heading out anyways," I blushed slightly.

"Don't worry about it, Castiel is-"

"That angel guy you were talking about, right? The tax accountant?" I cut in, laughing a little.

"Yeah, yeah, the one you met on Interstate 49," he nodded, smiling to see I remembered his friend.

"Dean, who's this again?" Sam cut in on our little conversation. I'd only met Sam twice, when I was on a hunt near the bar. I came in the first time and got wasted, only to come in the next morning to pay my tab with a walk of shame and most of the money in my wallet. We didn't really know each other that well.

"My friend, Sydney," he turned to his brother. "We, uh, met on the side of Interstate 49, that day I called you."

"So glad to see you haven't been talking about me," I chuckled.

"Oh, it's not like-"

"Kidding," I shook my head. "Alright, it's _actually_ late now, so I'm gonna go. Call me, Dean, I had a really good time tonight."

I leant up on my tiptoes once more and pecked his cheek before pulling back and smiling at Sam. "It was nice meeting you, the real you. I hope we can talk sometime, _Sam_," I smiled genuinely. I patted Sam's arm as I walked by and down the aisles of cars and into mine. As I drove away, I didn't hear Sam's confused question, "Seriously, Dean, who was that?"

The third time Dean and I met I called him. I was sitting in my motel room, sitting on hooker sheets, polishing my gun, and staring at my phone. It'd been eleven days – not that I was counting. Finally, I sat the rag in my hand on the bed and flipped open my phone. Nope, it was fully charged, and there were no missed calls. Or texts. Not even an email.

I bit my lip as I scrolled through my contacts. The blue light lit up Dean's name, taunted me, and finally I pushed talk. I put the phone between my shoulder and ear, and picked up the rag again. It rang five times before it was finally picked up. It wasn't Dean, though. It was a less deep voice, but still gruff. "Uh, yeah?"

"Is, um, Dean there?" I asked tentatively, hand stilling on my gun.

"He's a bit tied up at the minute, is this an emergency?" he questioned.

"Who is that?" a voice called in the background, a voice that sounded a whole lot like Dean.

"Who is this?" the man sighed.

"Oh, Sydney, Sydney Matthews, I was- I mean- I shouldn't have called, sorry," I started to close the phone, but the man on the other line stopped me, "Sydney? The girl that Dean's been talkin' about none stop for weeks now?"

"Um," I blushed, "Maybe?"

"Hang on a minute," there was shuffling before he came back. "The boy was just on a hunt, so make the conversation quick, girl."

"Yes sir," I agreed. As the phone was passed and Dean answered, I idly wondered who the _hell_ that had been.

"Hello?" Dean's voice was scratchy, like he needed to drink a lot of water and maybe cough up a lung.

"Dean? It's Sydney…Matthews," I added, in case he had forgotten the girl he met on the side of an interstate.

"Yeah, yeah, how've you been? Sorry I haven't called, we got a bit hung up on a hunt and I ended up getting myself in some trouble."

"Oh, don't be sorry," I rushed out. "I was, um… I kind of feel dumb for calling now, what with you being not even allowed to answer your own phone. I-I should just call back later-"

"No, don't hang up!" he stopped me. "I mean, it's just that…I've been on bed rest for the past forty-eight hours, no one to talk to but Bobby and Sam. I'm bored."

"Okay," I smiled, my hand moving on the gun again. "Who's Bobby?"

"Right, sorry, he's my uncle. Kind of like me and Sam's father," he explained.

"Dean, do you apologize like this to everyone?" I giggled, actually giggled. Yeah, I was ashamed of myself, too.

"Uh…honestly? No," he sighed into the phone. "I'm sorry," I could practically hear him kicking himself in the ass.

"Well, we'll have to work on that, then," I said, hand sliding over the hammer and down the handle of the weapon. "I just got done killing a were, and I thought, that…if you wanted to, or could- I mean, I know that it's like, the end of the world and all, but I just thought- well," I was ready to turn the gun around and use it on myself. I was stuttering like some sort of school girl!

"Sydney," he cut me off, an audible smirk coming through the phone.

"Yes?" I winced.

"Do you want to meet up again?"

It was still meet up at that point. It wasn't a date, because hunters really shouldn't get involved like that, but damn it if she didn't want him to ask her out on a date. "Sure," she answered quickly. "Where are you laid up at?"

"South Dakota," he answered. "Where are you?"

"Iowa, not too far," I grinned.

"Great," and he rattled off an address and some directions.

It took something like three hours to get to Sioux Falls, but when I pulled into Singer Salvage Yard, it all felt okay. When I spotted Dean's Impala, and I heard a dog barking off in the distance, I smiled. This was something that I was use to. Dogs, dirt, and cars. Those were all good things, things that didn't judge, things that you could cuddle, rub, play with, and it would be okay. It was a good mixture, most of the time, too.

As I parked my car and stepped out of the driver door, the dog in front of me barked a little louder. I held my hand out to him, showing him I wasn't going to harm him or his human. He sniffed me and then lapped at my hand happily. I grinned and rubbed his head, what a nice pup. I stepped away from the dog and up the steps. The place was a little rundown, nothing a little paint and wood work-

I stopped my train of thought quickly. Who was I to judge how this man lived? Who was I to believe that I could be friends enough with this man to even suggest some renovations? Yeah, I was either too tired or too stupid for my own good. I knocked against the screen door and waited until an older man with a graying beard and a trucker's cap answered the door in his wheel chair.

He eyed me before opening the second door and saying, "You that girl Dean's been talking about?"

"The one and only," I smiled. "Hopefully," I added, blinking a little extra at the thought.

He let out a short laugh and let me step inside. "Names Bobby, nice to meet ya."

"Ditto," I answered. "I'm Sydney."

"Well, the boy's down the hall in the kitchen. Him and that brother of his have been arguin' for the past hour, so don't be alarmed when you hear 'em shoutin'," he advised as I started down the hall he pointed out.

"Thanks," I nodded, and then I was stepping into the kitchen where an angry Dean stood. He was up against an old wooden table, glaring at his brother who leant against the kitchen counters with his arms crossed a sour look on his face. When he noticed me, the look upped to anger, and he turned away.

"Did I, uh, come at a bad time?" I asked, fidgeting with a piece of string hanging from my shirt.

"No, of course not, Sam and I just need to finish up talking for a second, and then we can talk," Dean flashed a quick smile before walking out of the room. Sam stood against the counter for a few more minutes before Dean snapped, "Sam!"

Sam walked out of the room slowly, taking his time. When he was gone I sat down in one of the rickety chairs- Damn it, I had to quit critiquing this man's home. What everyone else did and lived like was _not_ my business. As I was berating myself, the flapping of wings echoed through the room, and then a slightly balding man sat beside me. He smiled slightly and greeted me, "I'm Zachariah."

I stared at him for a few seconds before saying quietly, "The same Zachariah that sent Dean into the future?"

"Yes," he smiled wider. "So nice to hear Deano's been sharing. Now, what I would like to do is send you into that same future, so you can see how this, uh, little fling you two have going on will end."

"W-why would you want to do that?"

"Just so you can stop wasting your time," and he pressed his fingers to my forehead.

**Soo…what'd you think? Next chapter will be about Sydney going into the future. Dean, Cas, and Future-Sydney will be in it. Umm…review! Thank you soo much!**


	3. Back to the Future No Pun Intended

**Hi guys! So, here's the next update… Um… I hope this is good, I tried my best to keep everyone in character… Constructive criticism if you guys do review. Thanks. (:**

**Story Alert Thanks:**

**Bloody Scarlett Cherry Blossom**

**Luzleidys**

**AND A SUPER DUPER SPECIAL THANK YOU TO:**

**aj241985**

**FOR ADDING ME TO THEIR FAVORITE AUTHORS… THANK YOU! I have no idea if you added me to your favorite author because of this story, hehe. But otherwise, you are mentioned in here! (: Oh, and can I just say… I REALLY love your profile picture… (:**

**Alrighty, read on and prosper… I mean, salt and burn… I mean, uh, sorry for the rant?**

**Disclaimer: I do not own Dean, or Sam, or Cas… If I owned Dean though… Well, let's just say no one would get to see him for a long, long time. (AKA he would be in my bedroom, with me, unless that wasn't clear, hehe) And grumpy can join too, lmao.**

**Anywho… Enjoy!**

When I opened my eyes again I was face down in grass, a mouth full of dirt was spat out as I pushed up shakily. Forget dirt being 'good', when the stuff is in your mouth with worms and spiders crawling around, it freakin' sucks. I brushed off some of the dirt on my pants off and looked around the clearing I was in. There were no trees for miles.

I rubbed at my sore wrists and began walking, there was a rode and a large wall not too far off. I stepped up to the wall and looked around into the night air. "What the hell did that stupid angel do?" I muttered to myself, peeking through a gap in the metal.

Inside were several groups of people huddled around small fires, they all looked clean and were covered by blankets. Leaning against the closest building, which seemed to be a school house, was a woman with brunette hair. It covered her face and from the slight sniffles I could tell she was upset. I scratched at the back of my neck just as the woman did, and paused in the action.

The woman slowly looked up and out at the people, and I gasped. That was me, leaning against the wood cabin, crying. That was _me_ sitting not twenty feet away. I stepped back and onto a tin can. I bit my lip and prayed no one came out and shot me. Thankfully, no one seemed to notice me. I peered through the hole again and this time an eye met mine. I jumped back as the gate next to me swung open and I was met face to face with myself.

Instantly she was attacking me, swinging and clocking me in the eye. I stumbled back and exclaimed, "Wait! Wait!"

Instead she knocked me over the head with the butt of a gun, and I knocked out cold.

"Ow, what the fuck," I moaned, rubbing my head and blinking up at a hazy light bulb. When I noticed this wasn't the motel room I had fallen asleep in last night – shit, that was nearly two days ago – I looked around wildly.

She stood in the corner of the room, staring at me. I sat up, but didn't go too far. I was handcuffed to a bed railing. I cursed as I looked up at it and then back at, well, myself. "Look, I'm not a monster or anything-"

"I know, I already checked," she scratched at her ear. "I just don't know _how_ this is possible. I must have finally fallen off the deep end."

"No, you aren't- Um, we aren't crazy. I'm from the year 2009. Zachariah sent me-"

"Zachariah did this to you? Like he did to Dean?" she interrupted.

"Yes, just like he did to Dean," I nodded.

"What? Why would he-" she was cut off this time by a banging at the head door.

"Sydney! Cas' meet is starting!" it was a female voice, a scratchy deep female voice, but a female voice nonetheless.

"A-alright, Jane! I'll be out in a minute!" she hollered back, and when the boot stomps were no longer audible, she turned back to me. "You have to stay here, alright? Don't go picking any hand cuffs or screaming for help, because they'll kill you and me both, got it?"

"What? Why would they do that?" I demanded.

"We aren't too well liked around here," she said softly, before slipping out the door.

It felt like hours before she/I came back, damn that was giving me a headache. She barged through the door with a tight grimace and stared at me like I was some sort of puzzle she couldn't solve. Finally, she threw up her hands and exclaimed, "I don't know why you're here!"

"Well, I'm supposed to see how Dean and I's 'little fling' will end," I quoted the words as best as I could. "Could you uncuff me?"

"No," she snapped, crossing her arms over her chest. "I'm going to have to call Dean in here, aren't I?" she was speaking to herself, obviously. "We haven't talked to each other in a month, not since the last time we were forced to, at least."

"Why don't you guys talk anymore?" I leant forward.

"Doesn't matter, I'll be right back, wait here," she stepped out of the door before I could point out the obvious to her.

When she returned ten minutes later, I could hear her outside the door speaking to someone. "This is…well, it's crazy. You just have to go with it, though, because she isn't anything supernatural."

"Sydney, open the damn door," the deep voice, the deep, so familiar, voice ordered.

"Fine," she sighed, and the door squeaked open.

Dean stepped one foot inside before pausing. He stared at me while I stared right back. He was different, he was the same Dean, but aged times twenty. Hadn't Zachariah said it would only be five years? He stepped fully inside and under the dim light in the room. He had more scars and colder eyes, but inside him I could see a small flicker. In his beautiful eyes was a flicker of emotion.

"What is this?" he gestured to me with an open hand. "Is she a Shapeshifter?

"No, Dean, I ran all of the tests, I swear," she closed her eyes. "Zachariah did this to her."

"Zachariah," he shook his head. "That son of a bitch," he shook his head. "I should have ganked that mother when I had the chance."

"What are we going to do with her?" she finally broke the silence.

"Show her what she needs to be shown? Zachariah sent me back to try and change the future, maybe he sent her back to reinforce that?" he suggested, flicking his gaze back and forth between us.

"That isn't why she said Zachariah sent her here, Dean," Sydney shook her head, pony tail bobbing.

"Then why? Solve world peace?" he snarked.

"To see what our relationship was going to end up as," she spoke quietly, submissively.

"Can someone take off these handcuffs today?" I spoke up.

Dean turned his locked gaze from her to me, and shuffled over slowly. He grabbed the key off the table as he passed them, and unhooked my hands. I dropped them onto my lap and worked the circulation back into my abused wrists. It just wasn't their day.

"Maybe Cas will know something," I suggested after the silence began eating away at me.

"I doubt it," she said, instantly shutting her mouth again.

"It's still dark out, you two should go over to Cas' cabin and I'll meet up with you after I get back from my mission," Dean waved his hand, his voice lowered but no less demanding.

I scooted off the bed and over to myself, "Uh, lead the way."

She stepped outside the cabin and held a finger up to her lips as she led me behind the cabins and buildings to the third to last one in the line. She stepped up the stairs and I followed her. She pushed aside the beads there and inside. Castiel was sitting on the floor with a book in front of him. There was something very peculiar about the situation, I just couldn't put my finger on it.

"Cas," she greeted.

Castiel looked up at the both of us and frowned. "Again?"

"Yeah, except this time it's two of _me_ and not two of our fearless leader," the woman rolled her eyes.

"What year?" he asked, standing up and approaching me.

"Same one," she shook her head. "It's uncanny, really. I use to be damned beautiful."

"Oh, Syd, you still are," he smiled, laugh lines around his mouth.

She rolled her eyes and he said, "How long has it been since Dean was sent here?"

"Oh, um…a month?" I shrugged.

"Not much has changed-" he started.

"Well, everyone's alive, that's a change," she cut in.

"Yeah, yeah, I suppose," Castiel allowed, stepping back.

Three and a half hours later and all four of us sat at a dinky dining table under a single bulb. I stared at Dean, and then Castiel, and then at myself. I blinked slowly before cocking my head. I can't believe I hadn't thought of it already. The biggest piece of the puzzle was missing – literally biggest. I coughed to bring attention to myself, and asked, "Where's Sam?"

She looked down at her feet while Castiel scratched at his beard and looked away. Dean stared at me and shook his head, "How didn't I tell you any of this?"

"We've only know each other a month, and we've only actually met twice. I was just coming to meet up with you again, but you and Sam were arguing and then Zachariah showed up…" I trailed off.

"What were we arguing about?" he questioned.

"Uh, well… I don't know? You two left the room to finish up. Met Bobby for the first time, though," I revealed.

"Well, what I didn't tell you was that Sam…Sam said yes to Lucifer and he's now the devil," Dean said quickly, the words meshing together in a jumbled mess.

"W-what? Run that by me again?" I pushed up from the counter I was leaning against.

"Sam said yes, in Detroit-"

"That doesn't mean _anything_ to me," I cut her off. "I've only known this man for a few weeks. What the_hell_ do you mean your brother is the devil?"

"Why would Zachariah send her here without even knowing about Sam?" Dean asked, no one really answering him.

"Your _brother_, that giant assed man I met two weeks ago, is the fucking _devil_? What the _hell_!" I exclaimed, starting to pace the room. "Is the world ending? Is this my fault? Did Zachariah send me back to show me that our relationship is going to kill people? Are me and you even supposed to meet each other? What the _fuck_?"

"Hey, calm down," my future self said, stepping towards me.

"Oh, like you can give me any comfort! You're a mess yourself! I've only known _you_ for like three hours and already I know you're crazier than I am!"

"Hey!" she shouted, cutting off my ranting momentarily. "Calm the hell down!"

"No way, no way am I staying here. I just want to go back to my time and forget about all of this!"

Once again, I was seeing the butt of her gun coming down on my head. Bitch.

This time when I woke up I was alone in the room with myself, my future self, and I wasn't tied up. She stared at me silently, before saying, "Are you calmed down?"

"Yes," I whispered.

"There's some things you need to know before you start flipping out and really whacking out the past and future, okay?" she walked towards me, opting to sit in the wooden chair instead of next to me.

"O-okay," I agreed.

"First of all…" and she began explaining. She told me everything about Dean, and Sam, and even about Lucifer. I sat through all of it, taking it all in, and when she quieted, I shook my head.

"That's… I'm so sorry," I looked to myself. "That is one _hell_ of a rollercoaster."

"Yeah, and what you just did in front of Dean, that just broke his heart," she leant back on her chair.

"How so?"

"He probably figured since you were from the past you and him would have a better relationship, but…you just kind of ruined that idea-"

"Where is Dean?"

"Whoa, sit down," she pointed to the bed. I sat back down. "Are you calm enough to talk to him?"

"Yes, I am," I nodded quickly.

"Alright," she eyed me for a few more seconds before standing up and leaving. While she was gone I wandered through the small cabin. In the bathroom I found a jagged mirror and I fixed up my hair and smoothed out my clothes. When the door banged closed behind the new visitor, I walked back out.

Dean stood in the middle of the room uncomfortably, rubbing at the back of his neck and looking around the room. I bit my lip and cleared my throat. He turned towards me and tossed up a hand in greeting. I nodded back. We stood there for a few moments before I crossed the few feet between us and hugged him close to me. After a moment of hesitation he hugged me back, tightly.

His hands clung to the back of my back and mine wrapped around his waist. I buried my face in his shirt and breathed in his scent. He smelt like a mixture of lilacs and dirt, an interesting mixture that just somehow fit for someone like Dean. I pulled back slightly and looked up at him. Tears were swimming in his eyes, a first since I had met him.

I leant up on my toes and pressed my lips to his, not caring that this would be our second kiss, that I was in the future kissing a man I barely knew, and most definitely not caring that apparently we didn't have a good relationship. I pushed my tongue into his mouth this time, not giving him a chance, and ran my hands up his back to rest around his neck.

When my lungs were aching from no oxygen, and I was sure I had been thorough at discovering his mouth, I pulled back. I looked up into his eyes and whispered, "I-I want you, Dean, please."

He pressed his forehead to mine, our eyes still locked. I thought he might say no, but when his hands cupped the back of my thighs, and he raised my legs around his waist, I was positive he wanted - needed this as much as I did. A man I barely knew but felt like I knew for my whole life, walked me to the bed behind us, and sat me down.

I made quick work of his over coat, and then his under shirt followed. Under a dull bulb I looked at his magnificent chest. The scars and zags were nothing compared to the fading, red hand print on his shoulder. I pressed my hand to the print and looked up at him. He pressed his mouth back to mine, and we shared a rough kiss. It was all tongue, and teeth, and bruising force.

He pulled back to tear off my tank top and then unclasp my bra. I gasped when he pushed me down on the bed. I leant up on my elbows to watch as he stripped from his jeans and his shoes quickly. He climbed back up onto the bed and brought his weight down on my lightly. Just enough so I could feel the warmth, the muscle, the strength in his body.

He kissed down my neck and over my shoulder before reaching my chest. While he peppered kisses along my breasts and licked and nipped at my nipples, I pushed my hand under his boxers to grab at his ass. God, call me weird, but I was an ass girl. He groaned slightly when my hand slipped to the front and played with the bone that would lead to much greater things.

He kissed down my stomach, my hand pulling out of his underwear, and unbuttoned my shorts slowly. His fingers pulled down the zipper agonizingly sluggishly, at his own pace. When they were down my legs and he was hooking his fingers under the straps of my underwear, I looked down into his eyes. They were dark, darker than I'd ever seen a man's eyes go. I almost wondered if he was a demon, but of course that was silly.

He tore my shoes and my clothes off and then nipped at my thighs. I grabbed a handful of his hair and pulled him up for a kiss. While I licked and bit at his neck, sucking on his ear lobe even, I pushed his boxers down with my feet. He kicked them off the rest of the way and I wrapped my legs around his waist. We pulled back far enough to stare into each others eyes. He hesitated, I could see the question go across his handsome face, but I just whimpered, "Please," and that was enough for him.

He entered me slowly, and I moaned at the feeling. He stretched me open, wide enough to welcome him. I tightened around him when he reached the end and he pulled back out at a deliberate pace. While he continued his speed, I ran my hands along his back and ass, feeling all of his muscles and scars. He continued to keep eye contact with me, and I tried to, also, but my eyes opened and closed through his ministrations.

As he pumped a little harder and faster, I reached a hand up to his cheek and into his hair. "Oh, God,_Dean_," I panted, barely able to force the words out between gasps and moans.

"Sydney," he answered right back, hands running through my hair and over my body. His eyes searched mine for something, and I tried to show him how much this meant to me.

How much it meant to me that he was showing me I wasn't alone, didn't have to be afraid. He leant his forehead against mine once again, and as we reached our peaks, almost simultaneously, we cried each other's names out. He lay on top of me for a few passing minutes before pulling out and rolling over onto the other side of the bed. I lay staring up at the ceiling, panting, sweat sliding down my body. I rolled over and place my hand on his heart, my head resting on his shoulder where the burn was.

"Do we ever love each other, Dean?" I asked quietly.

He took in a deep breath and nodded slightly, "Yeah, we do. I mean…I still love you now, but there's just no way we can be together, y'know? The Apocalypse and Sam-"

He closed his mouth tightly. I ran my hand up and down his chest, over his stomach, and back up again. I waited for him to regain his composure, knowing he wouldn't want to cry or get upset after what we just did. Me for the first time, him…well, that was still an open question.

"Sammy and I, we just… I don't think I can ever love anyone after what happened. He was my brother, it's a different love, yeah, but… I wouldn't be able to stand it if I gave you that love, and you couldn't return it," he licked at his chapped lips and ran a hand through his hair.

I shivered slightly and pulled a sheet over us. "Did you tell the other Dean all of this?"

"No, no, of course not," he wrapped an arm around me, tucking me closer to him. "I just told him that we were lucky to ever get to meet you."

I kissed his pec softly and slipped my leg over his, huddling closer to him. "If it makes you feel any better, the Dean I know, he's a sweet, caring guy who looks after his brother and apologizes too much."

"Apologizes too much?" he repeated.

"Yeah," I giggled. "He says sorry in every sentence, I swear."

"Damn, I was a girl back then," he chuckled. The rumble went through his chest and into my ear. I smiled, content, and closed my eyes.

"Dean?" I whispered.

"Yeah?" he answered back in hushed tones.

I wanted to say so many things at that moment. I wanted to ask a million things, but instead, I just said, "I love you."

I almost didn't hear him say back, "I love you, too, Syd."

**Thanks for reading! Please review. Reviews are love and I really need some lovin'. I've got too much rejection from Sara and Eric lately… They still won't lemme have the guys, not even for five minutes! Some people, y'know?**

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	4. Reminiscing On the PastFuture

**One thing, so I know in 'The End' Dean says that Sam and him didn't start hunting together again, but in my story, they did. So, when it comes to that part down below, you have to keep that in mind!**

**Disclaimer: Not mine. L It makes me sad to think about.**

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**ELIZABETH ANGEL WINCHESTER – I really like your name! It's creative and made me smile when I got the email that said 'Elizabeth Angel Winchester added you to her favorite author list' Made my day! You're fantastic, and thanks!**

**PERIDOT809 – What can I say? You added me to your favorite story, story alert, and favorite author. I feel like I am now forever in your debt. I read the first chapter of your Vampire Diaries/Supernatural crossover story… (I'm not usually into Vampire Diaries) but your story is really good! It's well written and has me hooked. I'm gonna start reading it, lovely! Thanks soo much!**

As I blinked, just a bat of my eyelashes, I went from staring at the cabin door and hearing my past self and my Dean screwing, to staring into the eyes of a clean shaven Castiel. He glared at me and questioned, "How did you just appear?"

"What the hell is going on?" I barked, pushing up from the seat.

Dean, Sam, and Bobby appeared in the doorway, staring at me like I was crazy. "Dean, this is not your Sydney. This is the future Sydney."

"What? Cas, are you an angel again?" I questioned, starting to touch him, but stopping half way. I turned to look at Sam and reached for the gun not on me. "Is he possessed yet?"

"What? I-I'm not possessed," Sam backed up.

I untensed slightly and turned back to Castiel, "Cas, what's going on?"

Castiel seemed unsure why I was calling him by his nickname, but said, "Zachariah must have sent the wrong you back."

The fluttering of wings turned everyone's attention to the previous CEO of a fake business. He was smiling and clapped his hands together at the attention. "I didn't send the wrong girl back, Castiel. I meant to send this one here. The other one was a slow learner, she fornicated with the future Dean instead of resenting him like I planned. This version of the girl will be better in this time anyways."

And he was gone.

"Damn dick!" I shouted after him. I whirled on the three men in the doorway and said, "You have to get me back, I'm the only one that keeps your sorry ass from doing stupid shit."

"Whoa, you are a lot different, what happened?" Dean held his hands up defensively.

"I watched your future self get his neck snapped, you disappear thanks to another dick-Angel, listened to all of my friends die, and then all of it switches around as if it didn't happen! I'm a little crabby, so sue me!" I exclaimed, breathing harshly.

"Let's all calm down here," Bobby wheeled into the kitchen.

"Bobby," I gasped, hand fluttering up to my neck. "You-you're alive," I whispered, stepping over to him and bending down to hug him around shoulders. "_God_, it's been forever since I've seen you."

"Uh," he said uncomfortably, patting my back awkwardly. I pulled back and looked down at him with tear stricken eyes. "Jesus, you won't believe how hard it was to deal with Dumb and Dumber after you died."

"I _died_?" he gawked.

"Oh, fuck, you don't know, do you? Damn it all, you died saving Cas and Dean, aka Dumb and Dumber. It was heroic, I guarantee you that," I smiled, pulling away and standing up.

"Well, uh, good?" he cringed, pulling his cap away to scratch at his head.

"Fuck," I sighed. "I fucking hate 2009, it sucks."

"Wow, you adopted a sailor's mouth in the past mouth," Dean cracked.

"Go screw yourself," I rolled my eyes, not even glancing at him. "Bobby, do you know how I can get back to my time?"

"Well, uh," he looked towards his den. "I can check around. Cas, do you think you can zap her forward and bring the other back?"

"I do not believe so, Zachariah is stronger, he will have them locked, so to speak."

"Balls," Bobby griped, wheeling into his den.

I watched him go and then turned to the current Dumb and Dumber. I stared down Dean until he cocked an eye brow and then turned to Sam. I licked my bottom lip slowly, looking him over, before saying shortly, "Nice to see you not trying to kill me or anyone else, Samuel. It's a nice change of pace."

"Um, thanks?"

"It would be weird for me hug you, so just pretend I did," I advised, and turned back around to Castiel. "And boy did I forget how…different you were."

"My future self, as I have been told, is different than me. More…loose, I believe is the word Dean used," Castiel nodded.

"Yeah, loose," I snorted. "That's one way to put it. What am I supposed to do in this time? My past self doesn't have a half minded idea what to do in the future, God, all the kids are going to get a day off and they'll never want to go back."

"Pardon?"

"I'm the school teacher, you knew that, right?"

"Uh…no, sorry," Dean scratched at the side of his head. "I don't know a lot about you, actually."

"Did you just say sorry?" I questioned, a bit dumbfounded.

"Yes?"

"Been a damn long time since I've heard you say that," I snorted. "About you not knowing anything about me, well, I guess I'll have to clear that up, won't I?"

"If you don't mind," Dean smirked.

"One thing first, why were you two arguing?" I pulled out the kitchen chair behind me, sitting on it backwards so my chest was pressed to the head of the chair.

"How do you know about that?" Sam asked curiously.

"Hey, my past self may be a whore, but she did speak to Future-Dean and I before screwing him," I rolled my eyes.

"Yeah, about that…" Dean trailed.

"I have no idea why or how that happened, I knocked her out and then she woke up and wanted to talk to you, or, um, y'know, alone. So I got him and went over to Cas' cabin for a few minutes and I come back and they're going at it like wild bunnies. Just before I was going to turn around and leave, I'm staring into Cas' eyes and he's asking me how I just appeared."

"We, uh, we were just arguing about… Well, you, actually," Dean scratched the back of his neck, looking to his brother before back to me.

"Really? Lil' ole me? Why's that?"

"I'm gonna go help Bobby," Sam grumbled walking out of the room quickly.

I raised an eyebrow at Dean and waited for him to continue. "He doesn't really trust you, is all," he shrugged, moving into the kitchen and grabbing himself a chair. I turned mine around so I could sit on it appropriately and nodded.

"That's to be expected, we are hunters," I allowed. "Any particular reason why?"

"I don't know, I mean, it's Sam…that's got to mean something to _you_, doesn't it?" he sighed, rubbing a hand over his face.

"Well, considering I knew him as Keith for the first week of our meeting-"

"First _week_? I thought you two only knew each other from your visit to the bar he was at," Dean frowned.

"Oh, uh, that's how we met," I blushed slightly, surprised at myself. "But we hung out after that."

"Hung out as in…"

"God, Dean! We just hung out! We talked, drank, parted ways after a few weeks. We didn't…do anything," I laughed. Adding underneath my breath, "And that was all him."

"What?"

"Huh? I didn't say anything," I gave him my best innocent eyes.

"So, after that week who was he?" Dean questioned, leaning forward on the table.

"Samuel Winchester, bringer of the Apocalypse and in his own witness protection program hiding from hunters and his big brother," I reminisced. "He thought I was going to hit him, I'm pretty sure, but, y'know, we all mess up once. Just can't do it twice."

"You don't blame Sam for what he did?" his voice lowered considerably. "You may be the first hunter who doesn't, including him."

"Look, Dean, no one is a saint. Not you, not me, not even Bobby-"

"I heard that!" he hollered from the other room.

I smiled and continued, "We all make mistakes, we slip up on a hunt and someone gets hurt. We don't get somewhere fast enough and someone dies. We can't be held liable for every mishap that happens. If God held us responsible for every single mistake we made, no one would be in Heaven. I think, personally, that it isn't the fault that counts, it's what you do to fix it afterwards… Besides, you don't blame your brother."

He was quiet, staring at me or through me, one or the other. "You're right, I don't," he nodded. "After all," he licked his lips. "I started it in the first place."

"Oh, God! Puh-lease, you Winchesters can _never_ let something go, can you? Listen here, Dean, if you don't stop wallowing in the whole 'it's-my-fault-kill-me-now' suicide mission, I'll shoot you myself, you got it? Because I'll be damned if I go through it again!" I exclaimed, eyeing him with hard eyes.

"Alright, alright," he held his hands up. "I got you."

"Good," I sighed. "Now…where should I start? We met on the side of…Interstate 49, you were flying down it in your Impala and I was running out of the woods. You pulled over and you and Samuel climbed out. I must've looked like hell…"

"_Dean, pull over… I think there's a girl out there," Sam was squinting out of the Impala's windshield._

"_Where?" he pulled it to the side, eyeing the dark with major distrust._

_Suddenly, the woman Sam had seen was thrown on top of the hood of the car, a large beast on top of her. She struggled with it, landing a solid kick and throwing it off of her. She followed it down to the pavement, pulling out her gun only to have it knocked away. "Damn son of a bitch!" she shouted, scrambling to grab it up._

_She didn't even notice the two were there until Dean pulled out his gun and shot the were in the face. She looked up, surprised, and back to the dying creature. She accepted the hand Dean held out to her, and pulled herself up. "Wow, what luck, running into a pair of hunters just in the nick of time," she grinned, blood splattering her face and clothes._

_She shook Dean's hand, having still been holding it, and introduced herself, "Sydney, nice to meet you."_

"Not that different from how me and, uh, your past self met," Dean nodded.

"Well, you took me to drinks after that," I giggled. "And Samuel and I discussed how we had met. Then you noticed I was bleeding, and that wasn't just were blood. So you offered to take me back to your motel…"

"_And you think I'm that easy…why?" she had laughed, twirling her finger around the lip of the bottle of water she had in front of her._

"_Just to help you, sweetheart, nothing else," he winked._

_She admired his Impala as they neared it, Sam lagging in the back. "'67? It's a damn beauty."_

"_You know about cars?" he asked, surprised._

"_I've been in enough of them. I started out with thirty-five cents in my bank account, so I was hitch-hiking, naturally. After awhile, I started studying cars and stuff… It was a lot better than history."_

"_History?" he chuckled at the comparison._

"_Yep, Ms. Matthews, history extraordinaire," she had laughed. "I was a history college professor before I packed up and headed out. My school got attacked by some poltergeist and these nice men… John and Bobby, I'll never forget them. They came in and saved the day."_

"_John who?" he questioned suspiciously. They had reached the Impala._

"_Oh, uh, Winchester, I believe. Bobby Singer was the other man, do you know them?" she looked up at him hopefully. "I've wanted to thank the bastards for the longest time, but they left right after."_

"_John Winchester is our father," Sam was standing there then. "He died a few years ago-"_

"_Oh my God, I'm so sorry," she bowed her head. "That's terrible, he was a good man."_

"_Bobby isn't too far from here, if you want to meet him again," Dean offered._

"_Really?" she looked up at him, eyes shining with excitement._

"_Yeah, we need to regroup anyways," Dean nodded, much to his brother's shock._

"_That would be so great of you!" she threw her arms around his neck, wincing at the stretch around her shoulder and leg. She pulled back and bit her lip, "Sorry 'bout that, I'm… I'm a hugger."_

"_C'mon, we better get you stitched up," Dean's voice was gruffer as he walked around to the driver's seat._

_When the door was closed Sam stared down at the woman. "What are you trying to pull?"_

"_W-what are you talking about?" she half smiled, half frowned._

"_You aren't seriously going to try and act like you knew my dad, are you? Why didn't you bring it up before?" he demanded._

"_You weren't telling your life story, why should I have to?" she stepped back, reaching for the car door handle._

"_Right, so you just _forgot_ that you knew my dad, that it?"_

"_Look, Samuel, it isn't a happy story I tell a lot of people. Cool it, will ya?" she yanked open the door, slipping inside._

"You and Sam didn't get along at first," he stated.

"Nope, he hated me, actually…kind of like he does now," I laughed. "He got over it, after I was around for awhile, I mean, he didn't have much of a choice."

"So what happened after that?"

"Right, so… You got me stitched up, I spent the night in a room over with some poker winnings, and the next day we headed to South Dakota. When we got there Bobby recognized me after I reminded him how we met…"

_They were sitting around the den, Bobby at the desk, Sam leaning against the door, Dean on the sofa, and Sydney on a hard wooden chair. "…and you busted in the door right before the thing could choke me to death," she was finishing her story._

"_I remember that hunt, one of the first the boy's daddy and I had together. I remember you, specifically, though. You were the only one that wasn't flippin' out like you were under some terrorist attack. If I hadn't known better, I would have mistaken you for a hunter," he chuckled._

_She smiled at him. "You just up and left right after you got rid of it. No one in town knew where you went, and we were all ready to give you some money and maybe a couple of gold medals. Small towns have big hearts," she chided._

"_We had to get back to the kids," Bobby said sheepishly. "Sorry 'bout that."_

"_Oh, don't be. At least I'm still alive," she said cheerfully. Three days later, after she had healed up and the boys were itching for a hunt, she sat them down in the den again and said, "Do we part ways now?"_

"_I don't see why we have to," Dean smirked. "You seem to have held your own in the training exercises Bobby ran you through yesterday. If Sam is okay with it, I think you should tag along."_

_They both turned to him, waiting for the suspicious younger man to answer. "Why would I have a problem?" he gave his best smile._

"He had a problem," I shook my head. "In fact, the first hunt we had together, he almost got himself hurt because he didn't think I could do anything. So I saved his ass and got some well deserved respect. After that, we just kind of stuck together. Unfortunately, when you told me about your plan to ice the devil, I wasn't so gung-ho…"

"_Oh, so you _want_ to give the ex-junkie his fix! Really, Dean, because that sounds like the stupidest idea I've ever heard!" she shouted, shoving her things into her bag._

"_So you're just going to leave? Is that it? You're just going to leave after everything? I thought you trusted us!"_

"_Oh, screw you, Dean! Screw you! Of course I freakin' trust you, you asshole! I've trusted you enough to hunt with you, enough to let you kiss me, enough to let you be my damn boyfriend! You're the one with trust issues!" she accused, throwing a balled up t-shirt that belonged to him at his head._

_He caught it with one hand and cocked an eyebrow at her, "Really, Syd? _I'm_ the one with trust issues? You don't even let see what you write in that stupid journal you keep. If we're so close, what's to keep from me?"_

"_You want to know what I've been writing in it, Dean?" she demanded, pulling out clothes by the hand full until she found the leather bound book she jotted things down in. She threw the thing on the ground and stepped over it. "If you want to turn your brother back into a demon, go for it! See if I care!"_

_His eyes turned cold then, and he turned from her. "Just go," he whispered._

"_Dean…I-I didn't mean that," she reached out for his shoulder._

"_Just leave, Sydney," his voice was hard._

"_I'm sorry," she said softly, grabbing her bag and stepping out the door._

"Wow," he breathed.

"I fought dirty, Dean, I still can't believe I said that," I hung my head. "And you _have_ to know, I do not think of Samuel like that. I do _not_, I swear."

"It's okay," he nodded. "Keep going."

"_Sydney, open the damn door!" Dean was banging on the door._

_She shuffled over to it, eyes rimmed red and puffy from crying. "We have to go," he grabbed her shoulders, pushing her inside._

"_What happened? What's wrong?" she asked, panicked._

"_S-Sam said yes," Dean stuttered, stopping in his attempt to pack up her things._

"_What? That wasn't the plan!" she exclaimed. "He was just supposed to drink enough to kill him, not-"_

"_I know!" he cut her off. "Pack up," he ordered._

"And we built that camp. Cas lost his wings soon after and, yeah. Now I'm the school teacher for the camp, I teach everyone how it use to be with the books I packed and help out with math and other school stuff to my furthest extent."

"Wow," he repeated.

"Yep," I agreed. "Weird, I know."

"And…our relationship? How'd that end?"

"With that argument," I stated. "After that, you wanted nothing to do with me romantically, and it was mutual for me. The first time you talked to me was to ask if I could fill in for one of the hunters who dropped out of the line up for one of your missions. That was…a month after we made the camp."

"Damn."

"Yep."

-O-

**We join Sydney and Dean in the future next chapter. Please review, guys! I appreciate everyone who has put me on alert, I love you soo much for it! I would marry you all if I could! (:**


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